17461-09-5Relevant academic research and scientific papers
Synthesis of proline-derived dipeptides and their catalytic enantioselective direct aldol reactions: Catalyst, solvent, additive and temperature effects
Chen,Sung,Sung, Kuangsen
, p. 839 - 845 (2010)
A series of dipeptides of l-proline-l-amino acid and l-proline-d-amino acid were synthesized to evaluate the catalytic effect for asymmetric direct aldol reactions. In the direct aldol reaction, a catalyst of l-proline-l-amino acid achieves better enantioselectivity than the corresponding l-proline-d-amino acid catalyst. Solubility of the dipeptide catalysts in the solvents is a key point for achieving a better yield of the direct aldol reaction, while hydrogen bonding of solvent does not play an important role in attaining better enantioselectivity and yield. Yield and enantioselectivity of the direct aldol reaction in water were improved by NMM and SDS additives, but the results that were done in plain DMSO were even better.
Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction
Vlasserou, Ismini,Sfetsa, Maria,Gerokonstantis, Dimitrios-Triantafyllos,Kokotos, Christoforos G.,Moutevelis-Minakakis, Panagiota
, p. 2338 - 2349 (2018/04/06)
Peptides and especially prolinamides have been identified as excellent organocatalysts for the aldol reaction. The combination of prolinamides with derivatives bearing the 2-pyrrolidinone scaffold, deriving from pyroglutamic acid, led to the identification of novel organocatalysts for the intermolecular asymmetric aldol reaction. The new hybrids were tested both in organic and aqueous media. Among the compounds tested, 22 afforded the best results in petroleum ether, while 25 afforded the products in brine in high yields and selectivities. Then, various ketones and aldehydes were utilized and the products of the aldol reaction were obtained in high yields (up to 100%) with excellent diastereo- (up to 97:3 dr) and enantioselectivities (up to 99% ee).
